WordNet

first in order of importance; "the alpha male in the group of chimpanzees"; "the alpha star in a constellation is the brightest or main star"
the 1st letter of the Greek alphabet
the beginning of a series or sequence; "the Alpha and Omega, the first and the last, the beginning and the end"--Revelations
early testing stage of a software or hardware product; "alpha version"
any high mountain

PrepTutorEJDIC

アルファ(ギリシア語アルファベットの第1字A,α;英語のA,aに相当) / アルファ星(星座の主星)
高山,高峰

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/19 13:41:26」(JST)

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α-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. (The term "ketoglutaric acid," when not further qualified, almost always refers to the alpha variant. β-Ketoglutaric acid varies only by the position of the ketone functional group, and is much less common.)

Its anion, α-ketoglutarate (α-KG, also called oxo-glutarate) is an important biological compound. It is the keto acid produced by deamination of glutamate, and is an intermediate in the Krebs cycle.

Functions

Krebs cycle

α-Ketoglutarate is a key intermediate in the Krebs cycle, coming after isocitrate and before succinyl CoA. Anaplerotic reactions can replenish the cycle at this juncture by synthesizing α-ketoglutarate from transamination of glutamate, or through action of glutamate dehydrogenase on glutamate.

Formation of amino acids

Glutamine is synthesized from glutamate by glutamine synthetase, which utilizes an ATP to form glutamyl phosphate; this intermediate is attacked by ammonia as a nucleophile giving glutamine and inorganic phosphate.

Nitrogen transporter

Another function is to combine with nitrogen released in the cell, therefore preventing nitrogen overload.

α-Ketoglutarate is one of the most important nitrogen transporters in metabolic pathways. The amino groups of amino acids are attached to it (by transamination) and carried to the liver where the urea cycle takes place.

α-Ketoglutarate is transaminated, along with glutamine, to form the excitatory neurotransmitter glutamate. Glutamate can then be decarboxylated (requiring vitamin B₆) into the inhibitory neurotransmitter GABA.

It is reported that high ammonia and/or high nitrogen levels may occur with high protein intake, excessive aluminum exposure, Reye's syndrome, cirrhosis, and urea cycle disorder.

It plays a role in detoxification of ammonia in brain.^[2]^[3]^[4]

Relationship to molecular oxygen

Acting as a co-substrate, it also plays important function in oxidation reactions involving molecular oxygen.

Molecular oxygen (O₂) directly oxidizes many compounds to produce useful products in an organism, such as antibiotics, etc., in reactions catalyzed by oxygenases. In many oxygenases, α-ketoglutarate helps the reaction by being oxidized together with the main substrate. In fact, one of the α-ketoglutarate-dependent oxygenases is an O₂ sensor, informing the organism the oxygen level in its environment.

In combination with molecular oxygen, alpha-ketoglutarate is one of the requirements for the hydroxylation of proline to hydroxyproline in the production of Type 1 Collagen.

Antioxidant

α-Ketoglutarate, which is known to be released by several cell types, decreased the levels of hydrogen peroxide, and the α-ketoglutarate was depleted and converted to succinate in cell culture media.^[5]

Longevity

A study released on May 14, 2014 links α-ketoglutarate with significantly increased lifespan in nematode worms. ^[6]

Immune Regulation

A recent study has shown that α-ketoglutarate promotes TH1 differentiation and depletion of Glutamine (by depleting its metabolite α-ketoglutarate favors Treg differentiation. It might play a role in skewing the balance in favor of Tregs in the setting of amino acid deprivation that can be seen in the tumor microenvironment.^[7]

Production

α-Ketoglutarate can be produced by:

Oxidative decarboxylation of isocitrate by isocitrate dehydrogenase;
Oxidative deamination of glutamate by glutamate dehydrogenase.
From Galacturonic acid by the organism agrobacterium tumefaciens.^[8]

Alpha-ketoglutarate can be used to produce:

Creatine-alpha ketoglutarate

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|{{{bSize}}}px|alt=TCA Cycle edit]]

File:TCACycle WP78.png

TCA Cycle edit

^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

References

^ Merck Index, 13th Edition, 5320.
^ Does infectious fever relieve autistic behavior by releasing glutamine from skeletal muscles as provisional fuel?
^ Ott, P; Clemmesen, O; Larsen, FS (Jul 2005). "Cerebral metabolic disturbances in the brain during acute liver failure: from hyperammonemia to energy failure and proteolysis.". Neurochemistry international 47 (1-2): 13–8. doi:10.1016/j.neuint.2005.04.002. PMID 15921824.
^ Hares, P; James, IM; Pearson, RM (May–Jun 1978). "Effect of ornithine alpha ketoglutarate (OAKG) on the response of brain metabolism to hypoxia in the dog." (PDF). Stroke; a journal of cerebral circulation 9 (3): 222–4. doi:10.1161/01.STR.9.3.222. PMID 644619.
^ Long, L; Halliwell, B (2011). "Artefacts in cell culture: α-Ketoglutarate can scavenge hydrogen peroxide generated by ascorbate and epigallocatechin gallate in cell culture media.". Biochemical and biophysical research communications 406 (1): 20–24. doi:10.1016/j.bbrc.2011.01.091.
^ [1], doi:10.1038/nature13264
^ Klysz, Dorota; Tai, Xuguang (29 Sep 2015). "Glutamine-dependent α-ketoglutarate production regulates the balance between T helper 1 cell and regulatory T cell generation". Science Signaling (American Association for the Advancement of Science) 8 (396): ra97. doi:10.1126/scisignal.aab2610. Retrieved 14 October 2015.
^ Richard, Peter; Hilditch, Satu (2009). "d-Galacturonic acid catabolism in microorganisms and its biotechnological relevance". Applied Microbiology and Biotechnology 82 (4): 597–604. doi:10.1007/s00253-009-1870-6. ISSN 0175-7598.

UpToDate Contents

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Chatfield CH, Cianciotto NP.SourceDepartment of Microbiology and Immunology, Northwestern University Medical School, Chicago, IL, USA.
Methods in molecular biology (Clifton, N.J.).Methods Mol Biol.2013;954:151-62. doi: 10.1007/978-1-62703-161-5_7.
This chapter describes methods for culturing Legionella pneumophila in both complex and defined media. The first protocol describes the use of buffered charcoal yeast extract (BCYE) agar, the solid medium that is most commonly used for culturing L. pneumophila. The next procedure details the cultiva
PMID 23150393

Enhanced alpha-ketoglutaric acid production in Yarrowia lipolytica WSH-Z06 by regulation of the pyruvate carboxylation pathway.

Yin X, Madzak C, Du G, Zhou J, Chen J.SourceSchool of Biotechnology and Key Laboratory of Industrial Biotechnology, Ministry of Education, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu, 214122, China.
Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2012 Dec;96(6):1527-37. doi: 10.1007/s00253-012-4192-z. Epub 2012 Jun 9.
In previous research, a thiamine-auxotrophic yeast for alpha-ketoglutaric acid (KGA) overproduction was screened in our laboratory and named Yarrowia lipolytica WSH-Z06 (CCTCC no. M207143). However, the high concentration of by-products (mainly pyruvate) limited its application on an industrial scal
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Related Pictures

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★リンクテーブル★

リンク元	「alpha-ketoglutaric acid」
拡張検索	「alpha-ketoglutarate dehydrogenase」
関連記事	「ketoglutarate」「alpha」

「alpha-ketoglutaric acid」

α-Ketoglutaric acid^[1]
Names
	IUPAC name 2-Oxopentanedioic acid
	Other names 2-Ketoglutaric acid; alpha-Ketoglutaric acid; 2-Oxoglutaric acid; Oxoglutaric acid
Identifiers
CAS Number	328-50-7
ChEBI	CHEBI:30915
ChEMBL	ChEMBL1686
ChemSpider	50
DrugBank	DB02926
IUPHAR/BPS	3636
Jmol interactive 3D	Image
KEGG	C00026
MeSH	alpha-ketoglutaric+acid
PubChem	51
UNII	8ID597Z82X
	InChI InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) Key: KPGXRSRHYNQIFN-UHFFFAOYSA-N ; InChI=1/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) Key: KPGXRSRHYNQIFN-UHFFFAOYAN ;
	SMILES O=C(O)C(=O)CCC(=O)O ;
Properties
Chemical formula	C5H6O5
Molar mass	146.11 g/mol
Melting point	115 °C (239 °F; 388 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

αケトグルタル酸、αケトグルタール酸

関: alpha-ketoglutarate

「alpha-ketoglutarate dehydrogenase」

　　[★]

αケトグルタル酸脱水素酵素、αケトグルタル酸デヒドロゲナーゼ

関: ketoglutarate dehydrogenase complex

「ketoglutarate」

　　[★]

ケトグルタル酸、ケトグルタール酸

関: ketoglutaric acid

「alpha」

　　[★]

α、アルファ

関: alfa

[WikiPathways-9] The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

[1] Merck Index, 13th Edition, 5320.

[2] Does infectious fever relieve autistic behavior by releasing glutamine from skeletal muscles as provisional fuel?

[3] Ott, P; Clemmesen, O; Larsen, FS (Jul 2005). "Cerebral metabolic disturbances in the brain during acute liver failure: from hyperammonemia to energy failure and proteolysis.". Neurochemistry international 47 (1-2): 13–8. doi:10.1016/j.neuint.2005.04.002. PMID 15921824.

[4] Hares, P; James, IM; Pearson, RM (May–Jun 1978). "Effect of ornithine alpha ketoglutarate (OAKG) on the response of brain metabolism to hypoxia in the dog." (PDF). Stroke; a journal of cerebral circulation 9 (3): 222–4. doi:10.1161/01.STR.9.3.222. PMID 644619.

[5] Long, L; Halliwell, B (2011). "Artefacts in cell culture: α-Ketoglutarate can scavenge hydrogen peroxide generated by ascorbate and epigallocatechin gallate in cell culture media.". Biochemical and biophysical research communications 406 (1): 20–24. doi:10.1016/j.bbrc.2011.01.091.

[doi:10.1038.2Fnature13264-6] [1], doi:10.1038/nature13264

[DOI:10.1126.2Fscisignal.aab2610-7] Klysz, Dorota; Tai, Xuguang (29 Sep 2015). "Glutamine-dependent α-ketoglutarate production regulates the balance between T helper 1 cell and regulatory T cell generation". Science Signaling (American Association for the Advancement of Science) 8 (396): ra97. doi:10.1126/scisignal.aab2610. Retrieved 14 October 2015.

[RichardHilditch2009-8] Richard, Peter; Hilditch, Satu (2009). "d-Galacturonic acid catabolism in microorganisms and its biotechnological relevance". Applied Microbiology and Biotechnology 82 (4): 597–604. doi:10.1007/s00253-009-1870-6. ISSN 0175-7598.

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案内

alpha-ketoglutarate